Sodium Hydroxide → HCID 57647526, compound

HRID 1949020

Reaction equation

HRID 1949020 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.P(Br)(Br)[Br:15].P(Br)(Br)(Br)=O.[OH-].[Na+]>>[Br:15][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=[C:2]([NH2:1])[CH:11]=1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 24614Phosphorus tribromideHCID 178507935HCID 178507935, compound

Product 1

HCID 57647526HCID 57647526, compound

Conditions

Temperature
150 °C

Procedure

2-Amino-6-chloro-4-hydroxyquinoline (CAS 64319-84-2, 6.0 g, 31 mmol) were added portionswise to phosphorus tribromide (25 g, 92 mmol). Phosphorus oxybromide (10 g, 37 mmol) were added and the mixture was stirred at 150° C. for 16 h. The mixture was poured into 300 mL ice water and the pH was adjusted to 11 by addition of 32% sodium hydroxide solution. The solid was filtered off and washed with water and cyclohexane. 4-Bromo-6-chloro-quinolin-2-ylamine was obtained as a yellow solid (7.8 g, 98%), MS: m/e=258.9 (M+H+).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with water and cyclohexane

Sources & evidence

ORD record
ord-4c8d5ab21c224f2e87bfbbbbb28e4fe5
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Linked notes

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